Table of contents

1. A Review of General Chemistry5h 5m
2. Molecular Representations1h 14m
3. Acids and Bases2h 46m
4. Alkanes and Cycloalkanes4h 17m
5. Chirality3h 39m
6. Thermodynamics and Kinetics1h 22m
7. Substitution Reactions1h 48m
8. Elimination Reactions2h 30m
9. Alkenes and Alkynes2h 9m
10. Addition Reactions3h 19m
11. Radical Reactions1h 58m
12. Alcohols, Ethers, Epoxides and Thiols2h 42m
13. Alcohols and Carbonyl Compounds2h 17m
14. Synthetic Techniques1h 26m
15. Analytical Techniques:IR, NMR, Mass Spect7h 3m
16. Conjugated Systems6h 13m
17. Ultraviolet Spectroscopy51m
18. Aromaticity2h 34m
19. Reactions of Aromatics: EAS and Beyond5h 1m
20. Phenols55m
21. Aldehydes and Ketones: Nucleophilic Addition4h 56m
22. Carboxylic Acid Derivatives: NAS2h 51m
23. The Chemistry of Thioesters, Phophate Ester and Phosphate Anhydrides1h 10m
24. Enolate Chemistry: Reactions at the Alpha-Carbon1h 53m
25. Condensation Chemistry2h 9m
26. Amines1h 43m
27. Heterocycles2h 0m
28. Carbohydrates5h 53m
29. Amino Acids4h 20m
30. Peptides and Proteins2h 42m
31. Catalysis in Organic Reactions1h 30m
32. Lipids 2h 50m
33. The Organic Chemistry of Metabolic Pathways2h 52m
34. Nucleic Acids1h 32m
35. Transition Metals6h 14m
36. Synthetic Polymers1h 49m

11. Radical Reactions

Radical Reaction

Organic Chemistry

11. Radical Reactions

Radical Reaction

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4:00 minutes

Problem 11c

Textbook Question

Show how the following compounds could be prepared from 2-methylpropane:
c. 2-iodo-2-methylpropane

Verified step by step guidance

Start with 2-methylpropane (isobutane), which has the structure (CH₃)₂CHCH₃. The goal is to introduce an iodine atom at the tertiary carbon (C-2).

Perform a free radical halogenation reaction using chlorine (Cl₂) in the presence of UV light or heat. This will selectively form 2-chloro-2-methylpropane ((CH₃)₃CCl) due to the stability of the tertiary radical intermediate.

Next, carry out a nucleophilic substitution reaction (SN2) to replace the chlorine atom with iodine. Use sodium iodide (NaI) in acetone as the reagent. This reaction is driven by the insolubility of NaCl in acetone, which helps to shift the equilibrium toward the formation of 2-iodo-2-methylpropane ((CH₃)₃CI).

Ensure proper reaction conditions, such as maintaining a suitable temperature and reaction time, to maximize the yield of the desired product.

Finally, purify the product (2-iodo-2-methylpropane) using techniques such as distillation or recrystallization, depending on the physical properties of the compound.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Nucleophilic Substitution

Nucleophilic substitution is a fundamental reaction in organic chemistry where a nucleophile replaces a leaving group in a molecule. In the context of preparing 2-iodo-2-methylpropane from 2-methylpropane, this process typically involves the substitution of a halogen for a hydrogen atom, facilitated by a strong nucleophile such as iodide ion (I-). Understanding this mechanism is crucial for predicting the products of the reaction.

Radical Halogenation

Radical halogenation is a reaction that introduces halogens into organic compounds through radical intermediates. In the case of converting 2-methylpropane to 2-iodo-2-methylpropane, the process often begins with the formation of bromine or iodine radicals, which abstract hydrogen atoms from the alkane, leading to the formation of alkyl radicals. This concept is essential for understanding how to selectively introduce iodine into the desired position of the molecule.

Rearrangement Reactions

Rearrangement reactions involve the structural reorganization of a molecule to form a more stable or reactive species. In the synthesis of 2-iodo-2-methylpropane, understanding how carbocation rearrangements can occur is important, as the formation of a more stable tertiary carbocation can facilitate the substitution reaction. This concept helps in predicting the pathways and products of reactions involving branched alkanes.

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